Sealing the Deal, Part 1

Sealing the Deal, Part 1

She watched him toy with his ring as he berated her looking her steadily in the eye as he explained what a miserable job she had done negotiating a deal with a potential new client.

“Fortunately,” he said, winding down his quiet tirade, “the deal is not completely dead. But Mr. Jacobson has made his expectations very clear if this deal is to be closed. And Jessie,” he paused and even stopped fiddling with his ring, “this deal will be closed.”

She nodded and started to speak, but he waved his hand to silence her. “I know, I know,” he said. “You will do whatever it takes.”

He stood, pushing his chair back from his desk and turned to face the window. Jessie had always admired the view from Mr. Hamilton’s 17th floor office. It was a great grand sweep of the city, but right now she found she could focus only on his very obvious erection.

Mr. Hamilton continued to stare out the window. “I’m counting on you to do whatever it takes,” he said, “and with only a slight emphasis on the word ‘whatever.’”

She sat waiting expectantly, suddenly uncertain of what to do. It was clear she was going to spend some time with Mr. Jacobson satisfying whatever sexual needs he might have. She wondered if she would have to change into something sexier.

Jessie suddenly realized that Mr. Hamilton was standing next to her. When she turned in his direction, his hardon was nearly mouth level. He calmly unzipped his pants and pulled out his obviously hard cock. She was surprised by its size. Not only was he about 8″, but he was a little on the thick side. Mr. Hamilton was only a few inches taller than her 5’7” and had a nice build. The girls often talked about how well he wore his jeans and Jessie bet that he had a nice ass. She wondered if she would get to see it.

Mr. Hamilton stroked his cock, letting the head brush against her lips. “Now Mr. Jacobson,” he said quietly, “is a man who is exceptionally demanding as you’ve discovered through this negotiation process. He will expect to see you dressed as a career professional and yet behave like something of a slut. Now open.”

She opened her mouth as he put one hand on the back of her head and pushed himself deep in her mouth. He held her head as she gagged and continued to hold her head when the spasms passed. Slowly he started to thrust in and out of her mouth, his hand still firmly on her head.

“I’ve always admired your work, Jessie, though I will confess that I have always admired your ass too. I think your work can speak for itself and I plan to use you in many other contract negotiations.” He paused as he grunted and moan deeply. “God you have a tight mouth. I may use you for these kinds of negotiations too. In other words, my girl, I will use you in more conventional ways and… “. He stopped as he closed his eyes and fucked her mouth with a machine gun-like tempo. He slowed and thrust with slow, long pushes and then exhaled loudly as he came in her mouth and throat.

“Ahhh, god that was nice. I think Mr. Jacobson will be pleased.”

He stepped away from her, pushed himself back in his pants and zipped up. “Yes, if this deal closes the way it should, I will use you in many ways.”

Mr. Hamilton sat down again at his desk and adjusted his tie. He found a paper towel and handed to her so she could wipe off the cum around her mouth. Jessie was grateful she’d switched to waterproof mascara some time ago.

He looked at her directly again. “I don’t expect you just to be my cumslut though when I want you, you understand, I will have you.”

She nodded.

“Good,” he said. “You are a good lawyer and I expect you to have significant billable hours, but you seem to have other significant skills of which I plan to make very good and very profitable use. You understand?”

Again, she nodded.

“Excellent.” He slid a piece of paper across to her. She glanced at it and saw that it had Mr. Jacobson’s hotel and room number plus a time.

“Remember,” said Mr. Hamilton, “look like professional lawyer and behave like a slut. You may go.”

Jessie stood and started to say something, but Mr. Hamilton was already focused on his computer monitor. She left quietly and closed the door behind her.

She realized she was trembling and that she was now incredibly wet. She made her way back to her office and started to pack her briefcase. She glanced at her watch and realized she had about an hour before she had to meet Mr. Jacobson. She had time to go home and make a quick underwear change.

Jessie hurried into her bathroom and stripped off her clothes. She washed her pussy carefully glad she had shaved the day before. She rubbed some lotion on her pussy and just for a few moments, toyed with her clit. She was already tingling as she thought of Mr. Hamilton’s cock stretching her mouth.

She picked out a black lacy thong and its matching bra with lace sheer enough so her nipples could be seen. She put back on her gray silk blouse though left the top buttons undone so a hint of that lace might be seen if she were to bend over. She slipped back on her black suit and then decided she should also wear a garter and stockings as well as her 3” stilettos.

She checked herself once more in the mirror before leaving. She arrived at the hotel promptly and knocked firmly but quietly on the door of Mr. Jacobson’s hotel room. The door was opened almost immediately by a man she had never met and soon learned that Philip was Mr. Jacobson’s personal assistant. Watching the way he carried himself, she couldn’t wonder but how personal he might be.

Philip asked her to be seated. She took a few minutes to take in the elegance of this penthouse suite with its plush furniture in the living room, the rich furnishings, the crystal on the full bar. She glanced up as she heard Mr. Jacobson enter the room.

Unlike Mr. Hamilton, Mr. Jacobson was a man who exerted a tremendous aura of power. He stood about 6’2” and carried himself like the athlete he was. Though she had never seen him without a coat and tie, she sensed he was muscular. Tonight he was wearing what looked like silk pajama pants and a robe loosely tied at the waist. He was barefoot. She could see that he had a moderately hairy chest and wondered how it flowed down to his belly. Jessie found herself more aroused than she thought she might be in this potentially humiliating situation.

Mr. Jacobson sat on a couch across from her and held out his hand into which Philip silently placed a glass filled with a whiskey. “Good evening, Jessie,” he said. “Please stand up and turn around for me.”

She did as she was told and turned slowly for him.

“Very nice. Now remove your jacket, blouse, and skirt for me.”

She slipped out of her jacket as Philip moved around the room adjusting the lighting so that it was far more subtle though not what she would call romantic. She unbuttoned her blouse slowly and eased it off of her. She noticed a smile play at Mr. Jacobson’s mouth as he saw that lacy bra and could easily see that her nipples were already hard and erect. She unzipped her skirt, shimmied it down to the floor, and then stepped out of it.

“Ahh,” he said. “Very nice. Now turn again for me.”

She turned slowly and when turned to face him again she noticed that he had dropped one hand to his lap and was slowly stroking his cock through the silk of his pants.

“Come here,” he said and motioned that she was to kneel between his legs.

She walked over to him, her eyes never leaving his face, and slowly slipped to her knees.

He caressed her face. As he reached out to caress and fondle her tit, he said “I’m looking forward to this phase of our negotiations, Jessie. You do understand, of course, that you have no counterarguments in this discussion.” He pinched her nipple slightly, then harder. “You understand.”

“Yes, sir. I understand.”

A faint smile played on his lips. “That’s my good girl.”

He slipped his hand behind her head and pulled her face to his lap. “I think you’ll be able to see, my dear, that my dick needs some attention.”

She untied his robe and spread it open, then pressed her hands on his belly , her fingers fanned wide open. Then firmly moved her hands down his belly and to either side of his cock while leaning over and nuzzling his hardness through the soft fabric. As she massaged his balls and the skin around his cock, she opened her mouth and let her teeth ever so gently scrap across the shaft; she heard Mr. Jacobson inhale sharply. She put her hands on his waistband and pulled down; he lifted his hips so she could remove his pants. After she tossed them aside, she slowly kissed her way back up his legs, pushing them apart further until she once again reached his cock.

She opened her mouth wide and took the head of his cock in her mouth, tightening her lips around it and sucking hard. She heard him groan softly as she worked her tongue around his head and probed the slit. She felt his hand on the back of her hand and opened her mouth and throat as best she could knowing he would push her head down on his cock.

Like Mr. Hamilton, Mr. Jacobson held her head until the spasms subsided. “Look at me, Jessie,” she heard him say. She looked up at him.

“You will suck my cock until I have finished cumming.” He began to move his hips, his hand still at the back of her head. “Given my arousal and my need, that won’t take long this time. Then you will amuse me by sucking off Philip. And then when I am nearly ready again, you will take off all of your clothes so that I can fuck your pussy and your ass. I do not like a lot of noise, Jessie, so please no unnecessary noise to try to convince me you are enjoying yourself. I don’t care if you enjoy yourself. Your purpose tonight is to give me pleasure however I choose. Do you understand?”

She nodded as best she could. As he had been talking, his movements had quickened as had his breathing. He dropped his hand from the back of her head and leaned back, closing his eyes. “Finish me, bitch. Make me cum.”

She grabbed his shaft and began to stroke as she pushed and pulled with long hard sucks on his cock. It was only a few minutes later than he called out “oh my fucking god that’s good!” and came hard in her mouth. She gagged a little on his cum but swallowed hard and continued to suck until she was sure he was finished. She let him pop out of her mouth and moved his cock slightly to give a quick suck and lick of his balls. She heard him exhale with satisfaction.

“Philip,” he said, breathing a little hard yet. “Refill my drink first and then you may have her.”

Soon Philip was standing next to her and she moved so that she faced him. She could feel her pussy was creamy wet. Her clit throbbed.

Philip unzipped his pants and let them fall to the floor. He had a very healthy cock that already glistened. She could only imagine how arousing it might be for him to watch his boss fuck someone and she wondered again at how personal his services might be.

“Go ahead,” said Mr. Jacobson. “Suck him any way you like.”

She loved to play with the head of a man’s cock, so wrapped the head with her lips as she had done with Mr. Jacobson and worked the head with her tongue. She slipped one hand between Philip’s legs and massaged his balls as she held the shaft of his cock with the other. Philip adjusted his stance a little and she felt him gently thrust his hips towards her face.

“Suck his balls,” she heard Mr. Jacobson say and she immediately took Philip’s balls in her mouth and sucked them gently, then hard.

“Yes, very good. Now back to his cock, but spit on your fingers and lube up his asshole before you finger him.”

She did as she was told and heard Philip moan softly as she fingered his puckered hole.

“Go ahead, Philip,” she heard Mr. Jacobson say softly and she felt Philip’s hand on her head gently as he thrust a little harder in her mouth. She could hear how hard he was breathing and his soft comments under his breath.

She slipped a finger in his asshole and heard him groan a little more loudly and then heard him whisper, “Oh fuckin’ yes yes yes.”

Then she felt both of his hands on her head. She glanced up and saw that Philip’s eyes were closed as he slowly but firmly fucked her mouth. She slipped another finger in his asshole and held his hip with the other while she opened her mouth and throat for him. She felt him clinch around her fingers then heard him whisper “More” so she slid another finger in his asshole. He moaned again and clinched around her fingers, his rhythm as he fucked her face now a little faster and harder.

Soon she heard him groan loudly and he held her head to him and thrust hard one, two, three times, then held her head as he became perfectly still. “Holy fucking shit,” he said.

She heard Mr. Jacobson chuckle. “Yes, she has a very excellent mouth, doesn’t she? All right. You may put yourself back together Philip and I think Jessie needs a drink.”

Philip moved away from her, pulled up his pants, and put himself back together as he moved to the bar.

“You may sit down on the couch again, my dear.” Jessie stood slowly and carefully having been on her knees for quite a while. Soon Philip was handing her a glass of champagne. He was positioned in such a way that she could see him wink and say “thank you” before moving away to attend to Mr. Jacobson.

“Well,” said Mr. Jacobson, motioning towards his semi-erect penis, “that was quite stimulating. But I’ve changed my mind about wanting to fuck you just now, Jessie. I’m going to call Mr. Hamilton and let him know that we have a deal, but that I want you for further negotiation strategies. And that if I’m not as pleased with those results as I have been so far I will,” he chuckled at the joke he was about to make, “I’ll pull out of the deal.”

“I want you to go home, Jessie. Tomorrow you will return to me in a similar ensemble, but leave the thong at home. Just the bra, the garter, the stockings, and the heels. Please wear a suit as I don’t anyone thinking you are the slut you clearly can be. Be here promptly at 9A. I will have finished my international calls by then and will need a fuck. When you arrive, remove your suit and leave your clothes in a guest bathroom. Philip will show you where and then bring you to study. Plan to be here all day. Is that clear?”

Jessie nodded.

“Good. Get dressed and Philip will show you to the door. Join me in the study when she has left, Philip.”

With that, Mr. Jacobson stood, wrapped his robe back around himself, and strode out of the room. Jessie dressed quickly. As Philip showed her to the door, he said quietly so that she could barely hear: “He likes you very much which means he will take very good care of you. But I warn you he is demanding and his needs seem to be insatiable. See you tomorrow morning. Do not be late.”

And then she was out the door and it closed softly behind her.